Holiday Rentals in Massachusetts

61432 available vacation rental offers

7 nights
2
1
  • tripcom
  • booking
  • airbnb
  • tripadvisor
  • klook
  • agoda
  • expedia
  • hotelscom
  • hotelscombined
  • eztravel
  • makemytrip
  • rakutentravel
Massachusetts holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Massachusetts holiday rentals: compare the best deals

Best family friendly Massachusetts holiday rentals

Among the 61432 accommodations in Massachusetts, here are the 4 best family friendly rentals

Saint James Manor | Sleeps 20+ In Style & Comfort - Massachusetts
No reviews

Saint James Manor | Sleeps 20+ In Style & Comfort

apartment, Springfield
This 10-bedroom Victorian property is located in Springfield's historic McKnight district, offering easy access to the Basketball Hall of Fame (9.6 km), Springfield Museums (8 km), and MGM Springfield (11.2 km).
This spacious house accommodates up to 24 guests with 4.5 bathrooms, a fully equipped kitchen, high-speed Wi-Fi, a private fenced garden, and parking for four vehicles, with self check-in available.
Charming Harvard Victorian - Massachusetts
9.4 452 reviews

Charming Harvard Victorian

apartment, Cambridge
This Cambridge apartment is located just a short walk from Harvard Square and John F. Kennedy Park, making it perfect for exploring the city's vibrant cultural scene. The apartment boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment has five bedrooms and two bathrooms, comfortably accommodating up to ten guests. It offers a range of amenities, including a fully equipped kitchen, air conditioning, free Wi-Fi, and a patio with garden views, making it ideal for families and groups looking for a relaxing retreat.
Home Near Six Flags/ Hot Tub - Massachusetts
9.7 87 reviews

Home Near Six Flags/ Hot Tub

apartment, Agawam Town
This Agawam, Massachusetts property is located minutes from Six Flags New England, offering convenient access to the theme park.
Sleeping 10-11 guests, this three-bedroom house boasts a fully equipped kitchen, two bathrooms, a jacuzzi, and an indoor fireplace, alongside in-house laundry facilities.
7 Bed - Private Beach - Ocean Front W/boat Moorings - Fully Remodeled - Massachusetts
10 35 reviews

7 Bed - Private Beach - Ocean Front W/boat Moorings - Fully Remodeled

apartment, Plymouth
This Duxbury vacation home is located just two miles from Brown's Bank, Plymouth Long Beach, and the Myles Standish Monument State Reservation, making it a great base for exploring the area. The property has received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
This four-bedroom property spans 186 square metres and can accommodate up to ten guests. The house boasts a range of amenities including a fitness centre, tennis court, a terrace, a garden, and a fully equipped kitchen, offering a comfortable and enjoyable stay for families or groups of friends.

Top cities

Best pet friendly Massachusetts holiday rentals

Among the 61432 accommodations in Massachusetts, here are the 4 best pet friendly rentals

New! Family-friendly Getaway -1 Mi To Dtwn Salem W Roof Deck & Tiki Bar - Massachusetts
9.6 234 reviews

New! Family-friendly Getaway -1 Mi To Dtwn Salem W Roof Deck & Tiki Bar

apartment, Salem
This family-friendly apartment in Salem is conveniently located within walking distance of the downtown area, placing you close to shops, restaurants, and attractions like the Peabody Essex Museum and The House of the Seven Gables. The property has received excellent ratings for location, cleanliness, and overall experience.
The three-bedroom apartment offers ample space for up to 12 guests across its 1000 square metres. You'll enjoy modern amenities such as a fully equipped kitchen, air conditioning, a private garden, and a swimming pool, ensuring a comfortable and enjoyable stay.
Spacious Accessible Waterfront Retreat With Hot Tub - Massachusetts
9.7 3 reviews

Spacious Accessible Waterfront Retreat With Hot Tub

house, Orange
The Zen Waterfront Retreat is a three-bedroom house in Orange, Massachusetts, offering waterfront access with canoeing and fishing, situated approximately 34km from the Pelham Town Hall Historic District and 46km from the East Village Historic District.
This 196 square metre property boasts three bathrooms, two living rooms, sleeps up to 15 guests, includes free Wi-Fi, private parking, and air conditioning, making it ideal for families or large groups exploring the area.
Central 3br & Den Penthouse Boston Common Mgh & Tufts - Massachusetts
No reviews

Central 3br & Den Penthouse Boston Common Mgh & Tufts

apartment, Boston
This Boston flat is situated a 7-minute walk from the Freedom Trail, 1.2 kilometres from the Custom House, and 0.9 kilometres from the Old State House.
This 139 square metre penthouse offers accommodation for 11 guests, featuring a fully equipped kitchen, air conditioning, a fitness centre, and complimentary WiFi.
Hike & Explore Western Mass: Peaceful Studio - Massachusetts
10 2 reviews

Hike & Explore Western Mass: Peaceful Studio

studio, Palmer Town
This Palmer studio apartment is situated a 6-minute walk from Palmer Town Building and a 2-minute drive from the Quaboag River, offering convenient access to local amenities and attractions.
This 41 square meter studio accommodates two guests and features a full kitchen, air conditioning, and on-site parking, with the Indian Motorcycle Museum and Yankee Peddler nearby for cultural and shopping excursions.

Frequently asked questions about holiday rentals in Massachusetts

  • What are the must-see sights in Massachusetts?

    For must-see sights in Massachusetts, you've got plenty of options! Boston's Freedom Trail is a classic, taking you past historical landmarks like the Paul Revere House and Boston Common. Then there's Plymouth, where you can explore Plimoth Patuxet Museums and learn about the Pilgrims. For art and culture, the Museum of Fine Arts in Boston is world-renowned, and Salem offers a fascinating glimpse into the city's witch trial history. Don't forget the beautiful beaches on Cape Cod, like those in Chatham or Provincetown.
  • What are the best Airbnb and vacation rentals in Massachusetts?

    Near Boston Historic Two-bedroom With Modern Amenities, Steps To The Green Line & Minutes From Boston #15 and Luxurious Renovated House are the most popular Airbnb and vacation rentals in Massachusetts among travelers.

  • Are there unique natural phenomena in Massachusetts?

    Massachusetts boasts some lovely natural features. The Berkshires offer stunning mountain scenery, perfect for hiking. The coastline is dramatic, with places like the dramatic cliffs of Race Point Beach on Cape Cod. You can also explore the diverse ecosystems of the many state parks and forests, like the Mount Greylock State Reservation, home to the highest point in Massachusetts.
  • What are the most popular Airbnbs in Massachusetts?

  • What essentials should you bring along for a trip to Massachusetts?

    Pack for all types of weather! Massachusetts experiences varied conditions. Comfortable walking shoes are a must, especially if you plan on exploring Boston or hiking. Layers of clothing are recommended, as temperatures can change quickly. Don't forget sunscreen, a hat, and sunglasses, even on cloudy days. A reusable water bottle is also essential, especially during warmer months.
  • What are the best vacation rentals with a pool in Massachusetts?

  • What famous events or festivals are happening in Massachusetts?

    The Boston Marathon is a world-famous event held annually in April. Many smaller, local festivals take place throughout the year, celebrating everything from food to music. Check local listings for specific dates and events during your visit. The Fourth of July celebrations in many towns are also quite spectacular.
  • What are the best rentals for families and kids in Massachusetts?

  • Where can you find the best restaurants serving local dishes in Massachusetts, and what are the must-try specialties?

    For delicious local food, explore the North End in Boston for authentic Italian cuisine. You can find classic New England clam chowder and lobster rolls throughout the state. Many restaurants feature fresh seafood, given the state's coastal location. Trying a 'Boston cream pie' is a must for dessert lovers.
  • What are the best rentals or Airbnbs with a jacuzzi in Massachusetts?

  • What are some less-famous attractions in Massachusetts that are worth a visit?

    Consider visiting the charming town of Lenox in the Berkshires, known for its beautiful scenery and cultural attractions like Tanglewood. The Arnold Arboretum in Boston offers a peaceful escape, showcasing diverse plant collections. The Plimoth Patuxet Museums, while well-known for the Pilgrims, is a great place to experience living history. Also, explore the many lighthouses along the coast.
  • What are the best activities for engaging with locals and understanding their culture in Massachusetts?

    Visiting local farmers' markets is a great way to interact with locals and sample regional produce. Attending a local sporting event, like a Red Sox game, provides a taste of the city's passion. Exploring smaller towns outside of Boston gives you a chance to meet people and experience a slower pace of life. Many towns hold festivals and events that are perfect for cultural immersion.
  • What unique natural landscapes and terrain features can travellers explore in Massachusetts?

    Massachusetts offers a diverse range of landscapes. The sandy beaches of Cape Cod contrast sharply with the rocky coastline of the North Shore. The rolling hills of the Berkshires provide opportunities for hiking and scenic drives. The state also has numerous forests, wetlands, and ponds, offering diverse wildlife viewing opportunities. Don't forget the islands, like Martha's Vineyard and Nantucket.
  • How many days are ideal for a trip to Massachusetts, and what are some itinerary suggestions?

    A week is a good amount of time to explore Massachusetts, allowing you to see the main attractions in Boston and venture outside the city. A shorter trip of 3-4 days could focus on Boston and its surrounding areas. A possible itinerary could include 2 days in Boston, 1 day in Salem, and 2 days exploring Cape Cod or the Berkshires.

Nearby regions

Best Massachusetts holiday rentals with a pool

Among the 61432 accommodations in Massachusetts, here are the 4 best rentals with a pool

Luxury Boston Ranch Sleeps 8|pet+|heated Pool - Massachusetts
10 6 reviews

Luxury Boston Ranch Sleeps 8|pet+|heated Pool

apartment, Framingham
This Framingham holiday home, a spacious ranch-style property, is located approximately 48km from central Boston and 8km from the Natick Mall, offering easy access to both city attractions and shopping.
The 140 square metre dwelling boasts four bedrooms, two bathrooms, sleeping up to ten guests, and includes a fully equipped kitchen, game room with billiards and table tennis, a private swimming pool (open April 30th - September 30th), and four dedicated parking spaces.
Charming Groton Farmhouse Apartment - Massachusetts
8.0 1 review

Charming Groton Farmhouse Apartment

apartment, Groton
This Groton holiday home, a 13-minute drive (approx. 8km) from the MIT Haystack Observatory and 15-minute drive (approx. 9km) from Kimball Farm, offers a peaceful rural retreat near Beaver Brook Reservation and Silver Lake State Park.
The 102 square metre (1100 sq ft) property comprises one bedroom, one bathroom, a fully equipped kitchen including dishwasher, and a private garden with outdoor furniture; Wi-Fi, air conditioning, a fireplace, and on-site parking are also provided.
What A Gem City Views And A Rooftop Pool Await - Massachusetts
No reviews

What A Gem City Views And A Rooftop Pool Await

apartment, Boston
This Boston flat offers a prime location, a 14-minute walk to the Freedom Trail and 0.9 miles (approximately 1.45 kilometres) from Boston Common, placing you close to the Old State House and King's Chapel and Burying Ground.
This 70 square metre residence accommodates up to 9 guests, featuring air conditioning, a fully equipped kitchen with a dishwasher and oven, free Wi-Fi, a fitness centre, a rooftop pool with city views, and access to an on-site casino and water park.
Farmhouse Guest Apartment - Massachusetts
10 107 reviews

Farmhouse Guest Apartment

apartment, Groton
This one-bedroom apartment is located in a tranquil rural area of Groton, just a short distance from the town centre and a few kilometres from the picturesque Groton Long Point. It has received excellent ratings for location, cleanliness, and overall user experience.
The self-catering property has a private living room, full kitchen, bathroom, and a large bedroom with a desk, comfortably accommodating two guests. The apartment offers a swimming pool, BBQ area, and a garden, perfect for enjoying the beautiful weather and relaxing outdoors.

Best Massachusetts holiday rentals with parking

Upscale 4br Penthouse With Gym & Parking Near Mgh & Tufts - Massachusetts
8.0 7 reviews

Upscale 4br Penthouse With Gym & Parking Near Mgh & Tufts

apartment, Boston
This upscale Boston penthouse apartment is centrally located near South Station, a 6-minute walk away, offering easy access to the Freedom Trail and Boston Common (1.1km).
The 125-square-metre property boasts three bedrooms, two bathrooms, sleeps twelve guests, and includes a fully equipped kitchen, fitness centre, garden, parking, and free Wi-Fi.
Private Mother-in-law Apartment On The Lake! - Massachusetts
9.7 383 reviews

Private Mother-in-law Apartment On The Lake!

apartment, Hudson
This waterfront apartment in Hudson is just a short walk from the town centre, with its diverse range of restaurants and bars, and offers direct access to the lake with a private beach and dock. The property has received excellent ratings for location, cleanliness, and overall user experience.
The self-contained apartment, suitable for two guests, has its own kitchen and entrance, providing privacy and independence. Enjoy the lake with a paddle boat and kayaks, relax on the deck and patio, or gather around the fire pit in the evenings.
Aariz Nest - Massachusetts
10 1 review

Aariz Nest

apartment, Methuen Town
Aariz Nest, a private apartment in Methuen, is located 35 kilometres from Manchester Boston Regional Airport, 37 kilometres from the Mall of New Hampshire, and 39 kilometres from the Peabody Essex Museum.
This well-appointed flat offers 56 square metres of living space, featuring a fully equipped kitchen, air conditioning, a private balcony with quiet street views, and private on-site parking for up to five guests.
Your Home For The Holidays! - Massachusetts
9.9 960 reviews

Your Home For The Holidays!

apartment, Salem
This one-bedroom flat is conveniently located just 1.6 kilometres from Derby Street, the heart of Salem, and close to Salem State University. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The flat offers a comfortable and convenient stay for up to two guests. It features a fully equipped kitchen, private parking, air conditioning, and outdoor cameras for added security.
©2026 cozycozy.com